4 Key Challenges of Reentry

4 Key Challenges of Reentry

Let’s explore 4 key challenges and the solutions that Guest House provides to those challenges:

4 Key Challenges to Successful Reentry

Reentry refers to the movement of individuals out of prisons or jails back into the community. This transition is oftenprofoundly challenging, and successful reentry requires coordination and collaboration across multiple systems.

The mission of Friends of Guest House (Guest House) is to provide formerly incarcerated women the structure, supervision, support, and assistance they need to move beyond who they were to become who they want to be. We believe in women, families, and second chances—envisioning a world where your past does not define your future.

Challenge #1: Not Knowing Where to Begin

There are so many moving parts as a woman reenters our community post-incarceration – reconnecting with friends and family, finding a place to live, and finding work, to name but a few. It can be an overwhelming process to navigate.

Not knowing where to begin to rebuild one’s life is a significant challenge.

The key to overcoming this challenge is to provide reentering women with the resources they need to be successful. Guest House was founded in 1974 by parolee Betty McConkey, who, upon her release from prison, returned to Alexandria, VA where she resumed life with success thanks to a support system and access to housing and healthcare. Betty witnessed many fellow parolees struggle with no safety-net services for reentering women, and so she decided to act.

Services at Guest House originally included counseling, referrals, and a small residential program. Guest House has grown, from serving eight women to 300 women annually. This growth has included new housing opportunities for clients. In 2017, Guest House established its flagship Second Chance Community, a house that Aftercare residents can affordably rent on a transitional basis. In 2019, the organization opened a Residential program located in Alexandria, increasing our capacity by 15%. To date, Guest House has served more than 5,000 justice-involved women as they seek housing, employment, and life skills following incarceration.

Challenge #2: Family Strain

Many women rely heavily on their families for support and assistance as they transition. We’ve seen family after family step up to help make these transitions as smooth as possible.

Financial strain is named as one of the primary difficulties for families as they seek to support their recently released loved ones. But finances are just the start. Often, family members can experience higher levels of stress if their loved one has trouble finding a job, struggles with addiction, or has mental health issues.

Guest House’s six-month residential program offers a stable, supportive environment to reentering women as they begin to reintegrate into the community. Each woman is paired with a case manager, who works with them to create a tailored reentry plan. This is the ONLY 24/7 residential program for women reentering in Northern Virginia and is the largest such gender response program in the state.

60% of women in state prisons are mothers with minor children.

Family/community reconnection is one of the most important factors in successful reentry. Women who are reunited with their families, most notably their children, are less likely to return to prison. Friends of Guest House offers parenting classes and community connections so women can start to learn the tools and skills they will need to return to their children’s lives and build a strong, supportive community.

Challenge #3: Finding Employment

Though getting a job is often a requirement for parolees, it’s not a simple task. Instead, women often must explain the gap in their work experience by delving into why they were incarcerated. Hiring someone with a criminal record can cause some employers to pause.

According to the National Institute of Justice, 60% of those leaving prison do not find a job in the first year after their release. Even in cases where employers may express a willingness to hire individuals with criminal records, callback rates drop by 50% once this information is divulged. As a result, the reentry population is more likely to be in the process of seeking work; 93% are unemployed and actively seeking employment, compared to 84% of the population with similar financial backgrounds at large (Prison Policy, 2018).  

All Guest House residents are required to participate in our Workforce & Life Development (WLD) program to gain skills and prepare to return to the workforce. Upon completion of the program, graduates obtain career-focused employment with a liveable wage to support themselves and their families.

WLD is divided into four phases that progressively provide new and critical skills and experiences as women work toward reentering the workforce. Benchmarks are included along the way so that we can celebrate woman’s progress as they move through the program toward gainful employment.

Challenge #4: Mental Health Issues

For women with mental health and/or sobriety issues, the process of reentry is especially challenging.

While housing and employment are important factors that reduce the risk of recidivism for formerly incarcerated women, most are still coping with high exposure to trauma: 86% have experienced sexual violence, 77% intimate partner violence, 60% caretake abuse, 33% living with severe mental illness, and 80% living with drug or alcohol dependence.

Reentry programs, like Guest House, with case management infrastructure and a peer support network, are needed to provide the supportive infrastructure and skill-building required to reduce recidivism. Each resident is paired with a case manager who works with them to create a reentry plan and track weekly progress. Women are also paired with a trauma-informed Peer Support Specialist, an individual with lived experience of recovery for one-on-one as well as group work.


Guest House is proud of the fact that 85% of our graduates never return to incarceration and, in fact, get jobs and become contributing members of society. Measures of success for women upon completion of our Residential and Aftercare programs include the following:

  • 87% abstain from substance use & have a sobriety plan
  • 62% move to stable housing upon program completion
  • 82% are fully compliant with probation/parole terms; have successfully completed probation or parole in the past 6 months; or no active criminal justice involved over the past 6 months
  • 91% secure part-time, permanent employment with no benefits

Helpful links and resources:



5 Tips for Building Your Support Network After Prison Release